Efficient Synthesis of Amines by Iron‐Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination. Issue 6 (12th January 2018)

• Record Type: Journal Article
• Authors: Facchini, Sofia Vailati; Cettolin, Mattia; Bai, Xishan; Casamassima, Giuseppe; Pignataro, Luca; Gennari, Cesare; Piarulli, Umberto
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 6(2018)
• Page Start: 1054
• Page End: 1059
• Publication Date: 2018-01-12
• Subjects: Hydrogenation -- iron -- amination -- homogeneous catalysis -- imines; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701316
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Here we report the catalytic transfer hydrogenation (CTH) of non‐activated imines promoted by a Fe‐catalyst in the absence of Lewis acid co‐catalysts. Use of the (cyclopentadienone)iron complex1, which is much more active than the classical 'Knölker complex'2, allowed to reduce a number of N‐aryl and N‐alkyl imines in very good yields using i PrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe‐complex as the only catalyst has little precedents. Based on this methodology, we developed a one‐pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. Abstract :